Polina S. Zdereva, Grigorii V. Bezhenar, Anastasiya N. Sokolova, Boris V. Paponov, Andrey M. Rumyantsev, Elena V. Sambuk, Dmitry N. Maistrenko, Oleg E. Molchanov
{"title":"嘌呤核酸高氯酸盐与乙酰丙酮反应的意外产物导致 DNA 分子单链断裂","authors":"Polina S. Zdereva, Grigorii V. Bezhenar, Anastasiya N. Sokolova, Boris V. Paponov, Andrey M. Rumyantsev, Elena V. Sambuk, Dmitry N. Maistrenko, Oleg E. Molchanov","doi":"10.1007/s10593-024-03337-9","DOIUrl":null,"url":null,"abstract":"<p>The reactions of purine nucleic base perchlorates with the simplest 1,3-diketone – acetylacetone – were studied for the first time. It was demonstrated that adenine reacts with acetylacetone in a 1:2 molar ratio <i>via</i> opening of the pyrimidine fragment of the bicyclic struc- ture, elimination of a one-carbon fragment in the form of a formic acid molecule, and recyclization into 8-(4,6-dimethylpyrimidin-2-yl)- 2,4-dimethylimidazo[1,5-<i>a</i>]pyrimidine. Guanine, in turn, reacted with acetylacetone in a 1:1 ratio and formed 7,9-dimethyl-3<i>H</i>-pyrimido- [2,1-<i>b</i>]purin-10-ium-4-olate. In this case, the direction of heterocyclization differed from that observed in the reaction of guanine with malondialdehyde during the <i>in vitro</i> and <i>in vivo</i> formation of the minor nucleotide base M<sub>1</sub>G. The synthesized compounds were capable of causing single-strand breaks in DNA macromolecules.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"114 1","pages":""},"PeriodicalIF":1.4000,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Unexpected products of the reaction of purine nucleic base perchlorates with acetylacetone causing single-strand breaks in the DNA molecule\",\"authors\":\"Polina S. Zdereva, Grigorii V. Bezhenar, Anastasiya N. Sokolova, Boris V. Paponov, Andrey M. Rumyantsev, Elena V. Sambuk, Dmitry N. Maistrenko, Oleg E. Molchanov\",\"doi\":\"10.1007/s10593-024-03337-9\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>The reactions of purine nucleic base perchlorates with the simplest 1,3-diketone – acetylacetone – were studied for the first time. It was demonstrated that adenine reacts with acetylacetone in a 1:2 molar ratio <i>via</i> opening of the pyrimidine fragment of the bicyclic struc- ture, elimination of a one-carbon fragment in the form of a formic acid molecule, and recyclization into 8-(4,6-dimethylpyrimidin-2-yl)- 2,4-dimethylimidazo[1,5-<i>a</i>]pyrimidine. Guanine, in turn, reacted with acetylacetone in a 1:1 ratio and formed 7,9-dimethyl-3<i>H</i>-pyrimido- [2,1-<i>b</i>]purin-10-ium-4-olate. In this case, the direction of heterocyclization differed from that observed in the reaction of guanine with malondialdehyde during the <i>in vitro</i> and <i>in vivo</i> formation of the minor nucleotide base M<sub>1</sub>G. The synthesized compounds were capable of causing single-strand breaks in DNA macromolecules.</p>\",\"PeriodicalId\":9770,\"journal\":{\"name\":\"Chemistry of Heterocyclic Compounds\",\"volume\":\"114 1\",\"pages\":\"\"},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2024-08-22\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemistry of Heterocyclic Compounds\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1007/s10593-024-03337-9\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry of Heterocyclic Compounds","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s10593-024-03337-9","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Unexpected products of the reaction of purine nucleic base perchlorates with acetylacetone causing single-strand breaks in the DNA molecule
The reactions of purine nucleic base perchlorates with the simplest 1,3-diketone – acetylacetone – were studied for the first time. It was demonstrated that adenine reacts with acetylacetone in a 1:2 molar ratio via opening of the pyrimidine fragment of the bicyclic struc- ture, elimination of a one-carbon fragment in the form of a formic acid molecule, and recyclization into 8-(4,6-dimethylpyrimidin-2-yl)- 2,4-dimethylimidazo[1,5-a]pyrimidine. Guanine, in turn, reacted with acetylacetone in a 1:1 ratio and formed 7,9-dimethyl-3H-pyrimido- [2,1-b]purin-10-ium-4-olate. In this case, the direction of heterocyclization differed from that observed in the reaction of guanine with malondialdehyde during the in vitro and in vivo formation of the minor nucleotide base M1G. The synthesized compounds were capable of causing single-strand breaks in DNA macromolecules.
期刊介绍:
The international journal Chemistry of Heterocyclic Compounds publishes original papers, short communications, reviews, and mini-reviews dealing with problems in the field of heterocyclic chemistry in Russian and English. The Journal also publishes reviews and annotations on new books and brief reports on conferences in the field of heterocyclic chemistry, as well as commemoratives dedicated to prominent heterocyclic chemists.